rel-(1R,2S)-2-(methoxycarbonyl)cyclobutane-1-carboxylic acid

Base Information

• Chemical Name: rel-(1R,2S)-2-(methoxycarbonyl)cyclobutane-1-carboxylic acid
• CAS No.: 88335-88-0
• Molecular Formula: C₇H₁₀O₄
• Molecular Weight: 158.154
• Nikkaji Number: J1.459.836G
• Mol file: 88335-88-0.mol

Synonyms:88335-88-0;rel-(1R,2S)-2-(methoxycarbonyl)cyclobutane-1-carboxylic acid;(1S,2R)-2-methoxycarbonylcyclobutanecarboxylic acid;(1S,2R)-2-(methoxycarbonyl)cyclobutane-1-carboxylic acid;31420-52-7;(1r,2s)-rel-1,2-cyclobutanedicarboxylic acid, 1-methyl ester;SCHEMBL17887005;MFCD26516382;AKOS025290719;AT10515;AS-78887;CS-0055520;EN300-366101;cis-Cyclobutane-1,2-dicarboxylic acid monomethyl ester;(1S,2R)-2-methoxycarbonylcyclobutane-1-carboxylic acid;Cyclobutane-1beta,2beta-dicarboxylic acid 1-methyl ester;rac-(1R,2S)-2-(methoxycarbonyl)cyclobutane-1-carboxylic acid;(1S,2R)-2-METHOXYCARBONYL-CYCLOBUTANE-1-CARBOXYLIC ACID

Chemical Property of rel-(1R,2S)-2-(methoxycarbonyl)cyclobutane-1-carboxylic acid

Chemical Property:

• XLogP3: 0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 158.05790880
• Heavy Atom Count: 11
• Complexity: 187

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC(=O)C1CCC1C(=O)O
• Isomeric SMILES: COC(=O)[C@@H]1CC[C@@H]1C(=O)O

Technology Process of rel-(1R,2S)-2-(methoxycarbonyl)cyclobutane-1-carboxylic acid

There total 6 articles about rel-(1R,2S)-2-(methoxycarbonyl)cyclobutane-1-carboxylic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

methanol (67-56-1) + 3-oxabicyclo[3.2.0]heptane-2,4-dione (4462-96-8) → (cis)-(1RS,2SR)-cyclobutane-1,2-dicarboxylic acid monomethyl ester (31420-52-7,31420-60-7,35974-65-3,35974-69-7,88335-88-0,88335-89-1)

Guidance literature:

for 7h; Heating;

DOI:10.1016/S0957-4166(00)00297-4

Reference yield: 97.0%

methanol (67-56-1) + cis-1,2-cyclobutane dicarboxylic anhydride (4462-96-8) → (1S,2R)-cis-2-methoxycarbonyl-cyclobutane-1-carboxylic acid (88335-88-0)

Guidance literature:

With C₄₁H₂₁F₁₂N₂O₂PS; In toluene; at -35 ℃; for 36h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1002/anie.201000637

Reference yield: 88.0%

methanol (67-56-1) + 3-oxabicyclo[3.2.0]heptane-2,4-dione (4462-96-8) → (1S,2R)-cis-2-methoxycarbonyl-cyclobutane-1-carboxylic acid (88335-88-0)

Guidance literature:

With quinine; In tetrachloromethane; toluene; at -50 ℃; for 72h;

upstream raw materials:

methanol

3-oxabicyclo[3.2.0]heptane-2,4-dione

cis-1,2-cyclobutane dicarboxylic anhydride

Downstream raw materials:

(1S,2S)-methyl 2-(5-(4-bromophenyl)-1H-imidazol-2-yl)cyclobutanecarboxylate

((R)-3-methylmorpholino)((1,2-trans)-2-(5-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-imidazol-2-yl)cyclobutyl)methanone

((1,2-trans)-2-(5-(4-bromophenyl)-1H-imidazol-2-yl)cyclobutyl)((R)-3-methylmorpholino)methanone

(1,2-trans)-1-(2-(4-bromophenyl)-2-oxoethyl) 2-methyl cyclobutane-1,2-dicarboxylate